University Avenue on a Morning That Smells Like Ambition

Palo Alto's University Avenue runs from the Caltrain station to the gates of Stanford in a straight, tree-lined mile that contains more venture capital per square foot than any street in the world, and yet manages to feel like a pleasant college town rather than a financial district. The trick is the trees — massive London planes that shade the sidewalks and filter the California light into a dappled pattern that makes even a billion-dollar deal feel like a conversation at a cafe, which is where most of them happen anyway.

Coupa Cafe on Ramona Street, just off University, is the unofficial living room of Silicon Valley — a Venezuelan cafe where the coffee is strong, the arepas are genuine, and the tables have hosted so many startup pitches that the wood must absorb equity by osmosis. I come for the cortadito and stay for the people-watching: Stanford professors, VCs in vests, founders rehearsing their pitch decks to no one.

The bookstores are the antidote to the tech energy. Books Inc. on University has been selling physical books in the heart of the digital economy since before the internet existed, and the irony fuels the place with a cheerful defiance. The staff recommendations are handwritten, the shelves are curated with care, and the reading chair by the window catches the afternoon light in a way that makes screens seem like a less interesting technology.

Insider tip: Walk University Avenue to its end and cross Palm Drive onto the Stanford campus. The Main Quad — sandstone arches, red tile roofs, the Romanesque church at its center — is one of the most beautiful academic spaces in America, and it's open to the public, free, and five minutes from the best coffee in Silicon Valley.